7735-43-5Relevant academic research and scientific papers
Electroorganic synthesis 65. Anodic homocoupling of carboxylic acids derived from fatty acids
Weiper-Idelmann, Andreas,Aus Dem Kahmen, Martin,Schaefer, Hans J.,Gockeln, Marianne
, p. 672 - 682 (2007/10/03)
Fatty acid derived carboxylic acids with double bonds, hydroxy-, amino-, keto-, ester- and epoxy groups are anodically coupled to dimers (Kolbe electrolysis) in 29 to 81% yield and up to a 2.5 mol scale. Problems due to the low conductivity of fatty acid salts were overcome by the use of a flow cell with a narrow electrode gap. Fatty acids with branched alkyl chains gave dimers with interesting emulsifying properties. Dimethyl hexadecanedioate, accessible from methyl azelate, could be cyclized and further converted into homomuscone and muscone in a few steps. A commercial mixture of dimeric fatty acids (C36-dicarboxylic acids) has been coupled to give C70-diesters. Acta Chemica Scandinavica 1998. Part 64: Nielsen, M. F., Batanero, B.,.
An Approach to Cytochalasan Synthesis: Macrolide Formation by an Intramolecular Diels-Alder Reaction. X-Ray Structure of Methyl (1RS, 2SR, 5RS, 6RS)-2,5-Dimethyl-1-hydroxy-6-cyclohex-3-ene-1-carboxylate
Bailey, Stephen J.,Thomas, Eric J.,Vather, Sunil M.,Wallis, John
, p. 851 - 860 (2007/10/02)
When heated in toluene under reflux, under high dilution conditions, trans,trans-hexadeca-12,14-dienoyl-oxymaleic anhydride (4) cyclised via an intramolecular Diels-Alder reaction to give the macrocyclic lactone (5) in 27percent yield together with 5percent of a regioisomer (23). (1RS, 2SR, 5RS, 6RS)-2,5-Dimethyl-1-octanoyloxycyclohex-3-ene-1,6-dicarboxylic acid anhydride (11) was converted into the methyl (1RS, 2SR, 5RS, 6RS)-2,5-dimethyl-1-octanoyloxy-6-benzylcarbonylcyclohex-3-ene-1-carboxylate (33), but selective reduction of this ketone was unsuccessful.The structure of one of the reduction products, methyl (1RS, 2SR, 5RS, 6RS)-2,5-dimethyl-1-hydroxy-6-cyclohex-3-ene-1-carboxylate (35) was confirmed by an X-ray structure determination.
